JP2006506380A5 - - Google Patents
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- Publication number
- JP2006506380A5 JP2006506380A5 JP2004546268A JP2004546268A JP2006506380A5 JP 2006506380 A5 JP2006506380 A5 JP 2006506380A5 JP 2004546268 A JP2004546268 A JP 2004546268A JP 2004546268 A JP2004546268 A JP 2004546268A JP 2006506380 A5 JP2006506380 A5 JP 2006506380A5
- Authority
- JP
- Japan
- Prior art keywords
- triazol
- benzyl
- tetrahydro
- bipyridinyl
- ylmethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- -1 piperidindiyl Chemical group 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- FJPGWXXCNWQVFB-SFHVURJKSA-N (2r)-2-[3-methyl-5-(1-pyrimidin-2-ylpiperidin-4-yl)-1,2,4-triazol-4-yl]-2-phenylethanol Chemical compound N1([C@@H](CO)C=2C=CC=CC=2)C(C)=NN=C1C(CC1)CCN1C1=NC=CC=N1 FJPGWXXCNWQVFB-SFHVURJKSA-N 0.000 claims description 2
- WADYUFHRPDIVMM-UHFFFAOYSA-N 2-[4-(4-benzyl-5-butyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrimidine Chemical compound C=1C=CC=CC=1CN1C(CCCC)=NN=C1C(CC1)CCN1C1=NC=CC=N1 WADYUFHRPDIVMM-UHFFFAOYSA-N 0.000 claims description 2
- HWMADBAPMLYUFG-UHFFFAOYSA-N 2-[4-(4-benzyl-5-cyclopropyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrimidine Chemical compound C1CC1C1=NN=C(C2CCN(CC2)C=2N=CC=CN=2)N1CC1=CC=CC=C1 HWMADBAPMLYUFG-UHFFFAOYSA-N 0.000 claims description 2
- QCXGWFGGXDYTGG-UHFFFAOYSA-N 2-[4-(4-benzyl-5-methyl-1,2,4-triazol-3-yl)piperidin-1-yl]-4-methylpyrimidine Chemical compound C=1C=CC=CC=1CN1C(C)=NN=C1C(CC1)CCN1C1=NC=CC(C)=N1 QCXGWFGGXDYTGG-UHFFFAOYSA-N 0.000 claims description 2
- XUONHDZGZNJKLO-UHFFFAOYSA-N 2-[4-(4-benzyl-5-methyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrazine Chemical compound C=1C=CC=CC=1CN1C(C)=NN=C1C(CC1)CCN1C1=CN=CC=N1 XUONHDZGZNJKLO-UHFFFAOYSA-N 0.000 claims description 2
- VJXCWKBQOICZOM-UHFFFAOYSA-N 2-[4-(4-benzyl-5-methyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrimidine Chemical compound C=1C=CC=CC=1CN1C(C)=NN=C1C(CC1)CCN1C1=NC=CC=N1 VJXCWKBQOICZOM-UHFFFAOYSA-N 0.000 claims description 2
- JPUPXLNQXWYZPT-UHFFFAOYSA-N 2-[4-(4-benzyl-5-propan-2-yl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrimidine Chemical compound C=1C=CC=CC=1CN1C(C(C)C)=NN=C1C(CC1)CCN1C1=NC=CC=N1 JPUPXLNQXWYZPT-UHFFFAOYSA-N 0.000 claims description 2
- MWMWMHKJJNCLBF-UHFFFAOYSA-N 2-[4-(4-benzyl-5-propyl-1,2,4-triazol-3-yl)piperidin-1-yl]pyrimidine Chemical compound C=1C=CC=CC=1CN1C(CCC)=NN=C1C(CC1)CCN1C1=NC=CC=N1 MWMWMHKJJNCLBF-UHFFFAOYSA-N 0.000 claims description 2
- KVHBZEFFGFBZPQ-UHFFFAOYSA-N 2-[4-[4-benzyl-5-(2-methylpropyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyrimidine Chemical compound C=1C=CC=CC=1CN1C(CC(C)C)=NN=C1C(CC1)CCN1C1=NC=CC=N1 KVHBZEFFGFBZPQ-UHFFFAOYSA-N 0.000 claims description 2
- BIJLNARERPNZTM-UHFFFAOYSA-N 2-[4-[4-benzyl-5-[(2-chlorophenoxy)methyl]-1,2,4-triazol-3-yl]piperidin-1-yl]pyrimidine Chemical compound ClC1=CC=CC=C1OCC(N1CC=2C=CC=CC=2)=NN=C1C1CCN(C=2N=CC=CN=2)CC1 BIJLNARERPNZTM-UHFFFAOYSA-N 0.000 claims description 2
- BRAHJRKYAUITMC-UHFFFAOYSA-N 2-[4-[4-benzyl-5-[(4-fluorophenoxy)methyl]-1,2,4-triazol-3-yl]piperidin-1-yl]pyrimidine Chemical compound C1=CC(F)=CC=C1OCC(N1CC=2C=CC=CC=2)=NN=C1C1CCN(C=2N=CC=CN=2)CC1 BRAHJRKYAUITMC-UHFFFAOYSA-N 0.000 claims description 2
- NHCFGMIJJHVBBV-INIZCTEOSA-N 2-[4-[[5-methyl-4-[(1s)-1-phenylethyl]-1,2,4-triazol-3-yl]methyl]piperidin-1-yl]pyrimidine Chemical compound C1([C@H](C)N2C(=NN=C2C)CC2CCN(CC2)C=2N=CC=CN=2)=CC=CC=C1 NHCFGMIJJHVBBV-INIZCTEOSA-N 0.000 claims description 2
- BHBAJITZJZIHFJ-UHFFFAOYSA-N 4-(4-benzyl-5-methyl-1,2,4-triazol-3-yl)-1-phenylpiperidine Chemical compound C=1C=CC=CC=1CN1C(C)=NN=C1C(CC1)CCN1C1=CC=CC=C1 BHBAJITZJZIHFJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 6
- 208000005171 Dysmenorrhea Diseases 0.000 claims 5
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000004434 sulfur atom Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010007027 Calculus urinary Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000002177 Cataract Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 206010016654 Fibrosis Diseases 0.000 claims 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010021036 Hyponatraemia Diseases 0.000 claims 2
- 208000019693 Lung disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010029155 Nephropathy toxic Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010030043 Ocular hypertension Diseases 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 206010033314 Ovulation pain Diseases 0.000 claims 2
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims 2
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims 2
- 208000006399 Premature Obstetric Labor Diseases 0.000 claims 2
- 206010036600 Premature labour Diseases 0.000 claims 2
- 208000001647 Renal Insufficiency Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010047700 Vomiting Diseases 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 230000007882 cirrhosis Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000010643 digestive system disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 2
- 208000019622 heart disease Diseases 0.000 claims 2
- 230000009545 invasion Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 201000006370 kidney failure Diseases 0.000 claims 2
- 208000020816 lung neoplasm Diseases 0.000 claims 2
- 208000037841 lung tumor Diseases 0.000 claims 2
- 201000003152 motion sickness Diseases 0.000 claims 2
- 208000031225 myocardial ischemia Diseases 0.000 claims 2
- 230000007694 nephrotoxicity Effects 0.000 claims 2
- 231100000417 nephrotoxicity Toxicity 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 206010036596 premature ejaculation Diseases 0.000 claims 2
- 208000026440 premature labor Diseases 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- 208000020431 spinal cord injury Diseases 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- 208000019206 urinary tract infection Diseases 0.000 claims 2
- 208000008281 urolithiasis Diseases 0.000 claims 2
- 230000008673 vomiting Effects 0.000 claims 2
- 229940045860 white wax Drugs 0.000 claims 2
- HRGHFZCNGXYKSM-UHFFFAOYSA-N 1-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]pyrrolidin-3-ol Chemical compound C1C(O)CCN1CC(N1CC=2C=CC=CC=2)=NN=C1C1CCN(C=2N=CC=CC=2)CC1 HRGHFZCNGXYKSM-UHFFFAOYSA-N 0.000 claims 1
- IGYOBUDMQFDOGS-UHFFFAOYSA-N 1-[[4-benzyl-5-(1-pyrimidin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]piperidin-3-ol Chemical compound C1C(O)CCCN1CC(N1CC=2C=CC=CC=2)=NN=C1C1CCN(C=2N=CC=CN=2)CC1 IGYOBUDMQFDOGS-UHFFFAOYSA-N 0.000 claims 1
- KEEPLHBLESCVEN-UHFFFAOYSA-N 2-[4-[4-benzyl-5-(morpholin-4-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1N1CCC(C=2N(C(CN3CCOCC3)=NN=2)CC=2C=CC=CC=2)CC1 KEEPLHBLESCVEN-UHFFFAOYSA-N 0.000 claims 1
- JQWMVVHZFVVRGS-UHFFFAOYSA-N 2-[4-[4-benzyl-5-(morpholin-4-ylmethyl)-1,2,4-triazol-3-yl]piperidin-1-yl]pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1N1CCC(C=2N(C(CN3CCOCC3)=NN=2)CC=2C=CC=CC=2)CC1 JQWMVVHZFVVRGS-UHFFFAOYSA-N 0.000 claims 1
- WXOXVAQYBDLSRL-UHFFFAOYSA-N 2-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methoxy]ethanamine Chemical compound C=1C=CC=CC=1CN1C(COCCN)=NN=C1C(CC1)CCN1C1=CC=CC=N1 WXOXVAQYBDLSRL-UHFFFAOYSA-N 0.000 claims 1
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- KRMVZBILFSJMNJ-YDULTXHLSA-N 4-[[4-[(1S)-1-phenylethyl]-5-[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1,2,4-triazol-3-yl]methyl]morpholine trihydrochloride Chemical compound Cl.Cl.Cl.C1([C@H](C)N2C(=NN=C2CN2CCOCC2)CN2CCN(CC2)C=2N=CC=CC=2)=CC=CC=C1 KRMVZBILFSJMNJ-YDULTXHLSA-N 0.000 claims 1
- YENZIHDMDLNUBF-MLQCRBJCSA-N 4-[[4-[(1S)-1-phenylethyl]-5-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-1,2,4-triazol-3-yl]methyl]morpholine trihydrochloride Chemical compound Cl.Cl.Cl.C1([C@H](C)N2C(=NN=C2CN2CCOCC2)CN2CCN(CC2)C=2N=CC=CN=2)=CC=CC=C1 YENZIHDMDLNUBF-MLQCRBJCSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010012239 Delusion Diseases 0.000 claims 1
- 208000001362 Fetal Growth Retardation Diseases 0.000 claims 1
- 206010070531 Foetal growth restriction Diseases 0.000 claims 1
- 208000021891 Micturition disease Diseases 0.000 claims 1
- 208000027099 Paranoid disease Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- DENLVABGJNYKCR-UHFFFAOYSA-N benzyl 4-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(CC=2N(C(C3CCN(CC3)C=3N=CC=CC=3)=NN=2)CC=2C=CC=CC=2)CCN1C(=O)OCC1=CC=CC=C1 DENLVABGJNYKCR-UHFFFAOYSA-N 0.000 claims 1
- 230000003111 delayed effect Effects 0.000 claims 1
- 231100000868 delusion Toxicity 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 206010013990 dysuria Diseases 0.000 claims 1
- 208000030941 fetal growth restriction Diseases 0.000 claims 1
- 210000003754 fetus Anatomy 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 230000009593 intrauterine fetal growth Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- PKOMJEPAIAHLHI-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]-2-methoxy-n-methylethanamine Chemical compound C=1C=CC=CC=1CN1C(CN(C)CCOC)=NN=C1C(CC1)CCN1C1=CC=CC=N1 PKOMJEPAIAHLHI-UHFFFAOYSA-N 0.000 claims 1
- JCHXIGNAOIHLPB-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]-2-methoxyethanamine Chemical compound C=1C=CC=CC=1CN1C(CNCCOC)=NN=C1C(CC1)CCN1C1=CC=CC=N1 JCHXIGNAOIHLPB-UHFFFAOYSA-N 0.000 claims 1
- DRDVROHBUYOVDB-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]-3-methoxy-n-methylpropan-1-amine Chemical compound C=1C=CC=CC=1CN1C(CN(C)CCCOC)=NN=C1C(CC1)CCN1C1=CC=CC=N1 DRDVROHBUYOVDB-UHFFFAOYSA-N 0.000 claims 1
- QJZYCUPWKRRMME-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]-3-methoxypropan-1-amine Chemical compound C=1C=CC=CC=1CN1C(CNCCCOC)=NN=C1C(CC1)CCN1C1=CC=CC=N1 QJZYCUPWKRRMME-UHFFFAOYSA-N 0.000 claims 1
- LOVSZWVTDDBQLP-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]ethanamine Chemical compound C=1C=CC=CC=1CN1C(CNCC)=NN=C1C(CC1)CCN1C1=CC=CC=N1 LOVSZWVTDDBQLP-UHFFFAOYSA-N 0.000 claims 1
- KGEUFRXQLNRTOP-UHFFFAOYSA-N n-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl]methanesulfonamide Chemical compound C=1C=CC=CC=1CN1C(CNS(=O)(=O)C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 KGEUFRXQLNRTOP-UHFFFAOYSA-N 0.000 claims 1
- DNTOTJMNUBQSIZ-UHFFFAOYSA-N n-benzyl-2-[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]acetamide Chemical compound C=1C=CC=CC=1CNC(=O)CC(N1CC=2C=CC=CC=2)=NN=C1C(CC1)CCN1C1=CC=CC=N1 DNTOTJMNUBQSIZ-UHFFFAOYSA-N 0.000 claims 1
- LEMUDJYKMLDAIV-UHFFFAOYSA-N n-benzyl-2-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methoxy]acetamide Chemical compound C=1C=CC=CC=1CNC(=O)COCC(N1CC=2C=CC=CC=2)=NN=C1C(CC1)CCN1C1=CC=CC=N1 LEMUDJYKMLDAIV-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229940127234 oral contraceptive Drugs 0.000 claims 1
- 239000003539 oral contraceptive agent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- NZYAUFWFKCBCBS-HSZRJFAPSA-N tert-butyl (2r)-2-[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC[C@@H]1C(N1CC=2C=CC=CC=2)=NN=C1C1CCN(C=2N=CC=CC=2)CC1 NZYAUFWFKCBCBS-HSZRJFAPSA-N 0.000 claims 1
- HEZYZUKTRFWBDS-UHFFFAOYSA-N tert-butyl 2-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methoxy]acetate Chemical compound C=1C=CC=CC=1CN1C(COCC(=O)OC(C)(C)C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 HEZYZUKTRFWBDS-UHFFFAOYSA-N 0.000 claims 1
- WFQQCYBGBXMDMU-UHFFFAOYSA-N tert-butyl 2-[[4-benzyl-5-(1-pyridin-2-ylpiperidin-4-yl)-1,2,4-triazol-3-yl]methyl-methylamino]acetate Chemical compound C=1C=CC=CC=1CN1C(CN(CC(=O)OC(C)(C)C)C)=NN=C1C(CC1)CCN1C1=CC=CC=N1 WFQQCYBGBXMDMU-UHFFFAOYSA-N 0.000 claims 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0224919.1A GB0224919D0 (en) | 2002-10-25 | 2002-10-25 | Triazole compounds useful in therapy |
| PCT/IB2003/004587 WO2004037809A1 (en) | 2002-10-25 | 2003-10-14 | Triazole compounds for the treatment of dysmenorrhoea |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006506380A JP2006506380A (ja) | 2006-02-23 |
| JP2006506380A5 true JP2006506380A5 (enExample) | 2006-11-30 |
Family
ID=9946618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004546268A Withdrawn JP2006506380A (ja) | 2002-10-25 | 2003-10-14 | 月経困難症の治療用トリアゾール化合物 |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP1558598B1 (enExample) |
| JP (1) | JP2006506380A (enExample) |
| AT (1) | ATE367386T1 (enExample) |
| AU (1) | AU2003267791A1 (enExample) |
| BR (1) | BR0315676A (enExample) |
| CA (1) | CA2502932A1 (enExample) |
| DE (1) | DE60315062T2 (enExample) |
| ES (1) | ES2287508T3 (enExample) |
| GB (1) | GB0224919D0 (enExample) |
| MX (1) | MXPA05004305A (enExample) |
| WO (1) | WO2004037809A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9150567B2 (en) | 2009-10-01 | 2015-10-06 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE349449T1 (de) * | 2003-02-19 | 2007-01-15 | Pfizer | Für die therapie geeignete triazolverbindungen |
| GB0317227D0 (en) * | 2003-07-23 | 2003-08-27 | Pfizer Ltd | Treatment of male sexual dysfunction |
| GB0325021D0 (en) * | 2003-10-27 | 2003-12-03 | Pfizer Ltd | Therapeutic combinations |
| US7745630B2 (en) | 2003-12-22 | 2010-06-29 | Justin Stephen Bryans | Triazolyl piperidine arginine vasopressin receptor modulators |
| EP2316458A1 (en) * | 2004-09-20 | 2011-05-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| WO2006101521A2 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| US8071603B2 (en) | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| AP2007004047A0 (en) | 2005-01-20 | 2007-06-30 | Pfizer Ltd | Substituted triazole derivatives as oxtocin antagonists |
| EP1877399A1 (en) * | 2005-04-26 | 2008-01-16 | Pfizer Limited | Triazole derivatives as vasopressin antagonists |
| EP1885713A1 (en) | 2005-05-18 | 2008-02-13 | Pfizer Limited | 1, 2, 4 -triazole derivatives as vasopressin antagonists |
| JP2009513563A (ja) | 2005-06-03 | 2009-04-02 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ヒトのステアロイル−ＣｏＡデサチュラーゼ阻害剤としてのアミノチアゾール誘導体 |
| US7638541B2 (en) * | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| EP1958631A1 (en) * | 2007-02-14 | 2008-08-20 | AEterna Zentaris GmbH | Novel triazole derivatives as ligands of G-protein coupled receptors |
| CA2693169C (en) | 2007-07-19 | 2016-01-12 | Metabolex, Inc. | N-linked heterocyclic receptor agonists for the treatment of diabetes and metabolic disorders |
| US8288371B2 (en) | 2007-10-05 | 2012-10-16 | Pharmacopeia, Llc | Ortho pyrrolidine, benzyl-substituted heterocycle CCR1 antagonists for autoimmune diseases and inflammation |
| CA2802541A1 (en) | 2010-06-23 | 2011-12-29 | Metabolex, Inc. | Compositions of 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| EP2587919B1 (en) | 2010-07-01 | 2017-12-13 | Azevan Pharmaceuticals, Inc. | Methods for treating post traumatic stress disorder |
| US9006450B2 (en) * | 2010-07-01 | 2015-04-14 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical compositions and uses thereof |
| JP6129199B2 (ja) * | 2011-12-02 | 2017-05-17 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピペリジン誘導体、その医薬組成物及び使用 |
| EP3122743B1 (en) | 2014-03-28 | 2022-11-09 | Azevan Pharmaceuticals, Inc. | Compositions and methods for treating neurodegenerative diseases |
| WO2018026890A1 (en) | 2016-08-03 | 2018-02-08 | Cymabay Therapeutics | Oxymethylene aryl compounds for treating inflammatory gastrointestinal diseases or gastrointestinal conditions |
| IL273228B2 (en) | 2017-09-15 | 2025-04-01 | Azevan Pharmaceuticals Inc | Preparations and methods for treating brain injury |
| WO2019169193A1 (en) | 2018-03-01 | 2019-09-06 | Annapurna Bio Inc. | Compounds and compositions for treating conditions associated with apj receptor activity |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| CN116194441A (zh) * | 2020-07-23 | 2023-05-30 | 豪夫迈·罗氏有限公司 | 作为加压素受体v1 a拮抗剂的环己基取代的三唑 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE574944C (de) * | 1932-02-14 | 1933-04-21 | Schering Kahlbaum Ag | Verfahren zur Darstellung von 3, 4, 5-trisubstituierten 1, 2, 4-Triazolen |
| WO2001058880A1 (en) * | 2000-02-08 | 2001-08-16 | Yamanouchi Pharmaceutical Co., Ltd. | Novel triazole derivatives |
| EP1293503A4 (en) * | 2000-05-19 | 2008-04-02 | Astellas Pharma Inc | Triazole derivatives |
-
2002
- 2002-10-25 GB GBGB0224919.1A patent/GB0224919D0/en not_active Ceased
-
2003
- 2003-10-14 DE DE60315062T patent/DE60315062T2/de not_active Expired - Fee Related
- 2003-10-14 BR BR0315676-1A patent/BR0315676A/pt not_active IP Right Cessation
- 2003-10-14 CA CA002502932A patent/CA2502932A1/en not_active Abandoned
- 2003-10-14 AU AU2003267791A patent/AU2003267791A1/en not_active Abandoned
- 2003-10-14 MX MXPA05004305A patent/MXPA05004305A/es unknown
- 2003-10-14 ES ES03748487T patent/ES2287508T3/es not_active Expired - Lifetime
- 2003-10-14 EP EP03748487A patent/EP1558598B1/en not_active Expired - Lifetime
- 2003-10-14 AT AT03748487T patent/ATE367386T1/de not_active IP Right Cessation
- 2003-10-14 WO PCT/IB2003/004587 patent/WO2004037809A1/en not_active Ceased
- 2003-10-14 JP JP2004546268A patent/JP2006506380A/ja not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9150567B2 (en) | 2009-10-01 | 2015-10-06 | Cymabay Therapeutics, Inc. | Substituted tetrazol-1-yl-phenoxymethyl-thiazol-2-yl-piperidinyl-pyrimidine salts |
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